CH625397A5 - - Google Patents

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Info

Publication number: CH625397A5
Authority: CH; Switzerland
Prior art keywords: spp; propyl; ethyl; butyl; alkyl
Prior art date: 1976-01-28

Application number

CH83977A

Other languages

German (de)

English (en)

Inventor

Fritz Dr Maurer

Hans-Jochem Dr Riebel

Ingeborg Dr Hammann

Bernhard Dr Homeyer

Original Assignee

Bayer Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-01-28

Filing date

1977-01-24

Publication date

1981-09-30

1977-01-24 Application filed by Bayer Ag filed Critical Bayer Ag

1981-09-30 Publication of CH625397A5 publication Critical patent/CH625397A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 27
125000000217 alkyl group Chemical group 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 22
238000002360 preparation method Methods 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 14
238000000034 method Methods 0.000 claims description 12
238000009472 formulation Methods 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 9
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 8
230000000895 acaricidal effect Effects 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 7
230000000749 insecticidal effect Effects 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
230000001069 nematicidal effect Effects 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
229910052717 sulfur Chemical group 0.000 claims description 5
239000003513 alkali Substances 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
239000011230 binding agent Substances 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims description 2
239000002917 insecticide Substances 0.000 claims description 2
239000005645 nematicide Substances 0.000 claims description 2
241000251730 Chondrichthyes Species 0.000 claims 2
125000001309 chloro group Chemical group Cl* 0.000 claims 1
239000004480 active ingredient Substances 0.000 description 33
239000000460 chlorine Substances 0.000 description 29
239000002904 solvent Substances 0.000 description 23
-1 alkyl radical Chemical class 0.000 description 21
239000002689 soil Substances 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
239000003995 emulsifying agent Substances 0.000 description 15
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239000013543 active substance Substances 0.000 description 13
UJTMLNARSPORHR-UHFFFAOYSA-N oc2h5 Chemical compound C=C=[O+] UJTMLNARSPORHR-UHFFFAOYSA-N 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000003814 drug Substances 0.000 description 8
229940079593 drug Drugs 0.000 description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
241000244206 Nematoda Species 0.000 description 7
125000002877 alkyl aryl group Chemical group 0.000 description 7
239000012141 concentrate Substances 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
229920000151 polyglycol Polymers 0.000 description 7
239000010695 polyglycol Substances 0.000 description 7
239000000843 powder Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000007858 starting material Substances 0.000 description 6
AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 5
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000008187 granular material Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
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239000000969 carrier Substances 0.000 description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000254173 Coleoptera Species 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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206010061217 Infestation Diseases 0.000 description 3
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HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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239000013078 crystal Substances 0.000 description 3
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238000010438 heat treatment Methods 0.000 description 3
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CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
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CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
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XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
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NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
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150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
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239000004927 clay Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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238000004519 manufacturing process Methods 0.000 description 2
239000003921 oil Substances 0.000 description 2
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XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
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239000000047 product Substances 0.000 description 2
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241000500437 Plutella xylostella Species 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
241000908127 Porcellio scaber Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000193943 Pratylenchus Species 0.000 description 1
235000005805 Prunus cerasus Nutrition 0.000 description 1
241000722234 Pseudococcus Species 0.000 description 1
241001649229 Psoroptes Species 0.000 description 1
241000526145 Psylla Species 0.000 description 1
241001160824 Psylliodes Species 0.000 description 1
241000201375 Radopholus similis Species 0.000 description 1
241001509970 Reticulitermes <genus> Species 0.000 description 1
241000722249 Rhodnius prolixus Species 0.000 description 1
241001510236 Rhyparobia maderae Species 0.000 description 1
241000318997 Rhyzopertha dominica Species 0.000 description 1
241000316887 Saissetia oleae Species 0.000 description 1
241000509416 Sarcoptes Species 0.000 description 1
241000253973 Schistocerca gregaria Species 0.000 description 1
241000522594 Scorpio maurus Species 0.000 description 1
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239000004113 Sepiolite Substances 0.000 description 1
241000258242 Siphonaptera Species 0.000 description 1
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241000985245 Spodoptera litura Species 0.000 description 1
241001494139 Stomoxys Species 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
241000883295 Symphyla Species 0.000 description 1
241000255626 Tabanus <genus> Species 0.000 description 1
241001065719 Tetranychus ludeni Species 0.000 description 1
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241001414989 Thysanoptera Species 0.000 description 1
241000511627 Tipula paludosa Species 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
241001238451 Tortrix viridana Species 0.000 description 1
241000018137 Trialeurodes vaporariorum Species 0.000 description 1
241001414833 Triatoma Species 0.000 description 1
241000254086 Tribolium <beetle> Species 0.000 description 1
241001259047 Trichodectes Species 0.000 description 1
241000255993 Trichoplusia ni Species 0.000 description 1
241000267823 Trogoderma Species 0.000 description 1
241001267621 Tylenchulus semipenetrans Species 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
235000013447 Xanthosoma atrovirens Nutrition 0.000 description 1
240000001781 Xanthosoma sagittifolium Species 0.000 description 1
241000353223 Xenopsylla cheopis Species 0.000 description 1
241000201423 Xiphinema Species 0.000 description 1
241001466337 Yponomeuta Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
241001414985 Zygentoma Species 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
150000008052 alkyl sulfonates Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
230000012173 estrus Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000004088 foaming agent Substances 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
239000000446 fuel Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000003502 gasoline Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000001023 inorganic pigment Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
230000001418 larval effect Effects 0.000 description 1
229920000126 latex Polymers 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
239000004579 marble Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
SYBYTAAJFKOIEJ-UHFFFAOYSA-N methyl iso-propyl ketone Natural products CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
229920005615 natural polymer Polymers 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000011368 organic material Substances 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
239000001007 phthalocyanine dye Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000003380 propellant Substances 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
239000003531 protein hydrolysate Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
230000000391 smoking effect Effects 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
235000011182 sodium carbonates Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/28—Cinnolines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/20—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650905—Six-membered rings having the nitrogen atoms in the positions 1 and 2

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CH83977A 1976-01-28 1977-01-24 CH625397A5 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2603052A DE2603052A1 (de)	1976-01-28	1976-01-28	S- eckige klammer auf 1,6-dihydro- 6-thioxo-pyridazin-(1)ylmethyl eckige klammer zu -(thiono)-(di)-thiol-phopshor(phosphon)- saeureester- bzw. -esteramidderivate, verfahren zur ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide

Publications (1)

Publication Number	Publication Date
CH625397A5 true CH625397A5 (fr)	1981-09-30

Family

ID=5968406

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH83977A CH625397A5 (fr)	1976-01-28	1977-01-24

Country Status (20)

Country	Link
US (1)	US4097593A (fr)
JP (1)	JPS5291884A (fr)
AT (1)	AT350324B (fr)
AU (1)	AU503845B2 (fr)
BE (1)	BE850798A (fr)
BR (1)	BR7700494A (fr)
CH (1)	CH625397A5 (fr)
CS (2)	CS191350B2 (fr)
DD (1)	DD128688A5 (fr)
DE (1)	DE2603052A1 (fr)
DK (1)	DK141334C (fr)
FR (1)	FR2339619A1 (fr)
GB (1)	GB1521952A (fr)
IL (1)	IL51324A (fr)
NL (1)	NL7700792A (fr)
PL (1)	PL101197B1 (fr)
PT (1)	PT66103B (fr)
SE (1)	SE7700853L (fr)
TR (1)	TR19269A (fr)
ZA (1)	ZA77479B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2843823A1 (de)	1978-10-07	1980-04-24	Bayer Ag	N-iso-propyl-s-(1,6-dihydro-6-(thi) oxo- pyriezin(1)-yl-methyl)-thiolphosphorsaeure- esteramide, verfahren zu ihrer herstellung und ihre anwendung als schaedlingsbekaempfungsmittel

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2938902A (en) *	1959-04-24	1960-05-31	American Cyanamid Co	Novel pyridazinones and methods of preparing same
CH547313A (de) *	1968-02-02	1974-03-29	Bayer Ag	Verfahren zur herstellung von phosphor-, phosphon-thionphosphor- oder thionsphosphonsaeureestern- bezw.-esteramiden.
DE2046088A1 (de) *	1970-09-18	1972-03-30	Farbenfabriken Bayer Ag, 5090 Lever Kusen	Cinnolinyl(thiono)phosphor(phosphon) säureester und esteramide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akanzide
DE2316821A1 (de)	1973-04-04	1974-10-17	Bayer Ag	S- eckige klammer auf 1,6-dihydro-6oxo-pyridazin-(1)ylmethyl eckige klammer zu -(thiono)-(di)-thiol-phosphor(phosphon)saeureester- bzw. -esteramidderivate, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide
DE2348736A1 (de) *	1973-09-28	1975-04-10	Bayer Ag	S- eckige klammer auf 1,6-dihydropyridazin-(1)-ylmethyl eckige klammer zu -thiolphosphorsaeureester- bzw. -esteramidderivate, verfahren zu ihrer herstellung sowie ihre verwendung als nematizide

1976
- 1976-01-28 DE DE2603052A patent/DE2603052A1/de not_active Withdrawn
1977
- 1977-01-10 US US05/758,242 patent/US4097593A/en not_active Expired - Lifetime
- 1977-01-21 PT PT66103A patent/PT66103B/pt unknown
- 1977-01-24 CH CH83977A patent/CH625397A5/de not_active IP Right Cessation
- 1977-01-25 CS CS781679A patent/CS191350B2/cs unknown
- 1977-01-25 CS CS77506A patent/CS191327B2/cs unknown
- 1977-01-25 GB GB2964/77A patent/GB1521952A/en not_active Expired
- 1977-01-25 TR TR19269A patent/TR19269A/xx unknown
- 1977-01-25 IL IL51324A patent/IL51324A/xx unknown
- 1977-01-26 AU AU21679/77A patent/AU503845B2/en not_active Expired
- 1977-01-26 JP JP689077A patent/JPS5291884A/ja active Pending
- 1977-01-26 DD DD7700197100A patent/DD128688A5/xx unknown
- 1977-01-26 NL NL7700792A patent/NL7700792A/xx not_active Application Discontinuation
- 1977-01-27 BE BE174414A patent/BE850798A/fr unknown
- 1977-01-27 BR BR7700494A patent/BR7700494A/pt unknown
- 1977-01-27 ZA ZA770479A patent/ZA77479B/xx unknown
- 1977-01-27 DK DK34377A patent/DK141334C/da active
- 1977-01-27 SE SE7700853A patent/SE7700853L/xx unknown
- 1977-01-27 PL PL1977195606A patent/PL101197B1/pl unknown
- 1977-01-28 AT AT53377A patent/AT350324B/de not_active IP Right Cessation
- 1977-01-28 FR FR7702490A patent/FR2339619A1/fr active Granted

Also Published As

Publication number	Publication date
DK34377A (da)	1977-07-29
BR7700494A (pt)	1977-10-04
IL51324A (en)	1979-11-30
DE2603052A1 (de)	1977-08-04
IL51324A0 (en)	1977-03-31
DK141334B (da)	1980-02-25
ATA53377A (de)	1978-10-15
FR2339619B1 (fr)	1980-07-11
CS191350B2 (en)	1979-06-29
DD128688A5 (de)	1977-12-07
NL7700792A (nl)	1977-08-01
TR19269A (tr)	1978-10-06
DK141334C (da)	1980-08-18
AU503845B2 (en)	1979-09-20
US4097593A (en)	1978-06-27
PT66103B (de)	1978-06-27
AT350324B (de)	1979-05-25
PT66103A (de)	1977-02-01
JPS5291884A (en)	1977-08-02
AU2167977A (en)	1978-08-03
GB1521952A (en)	1978-08-23
CS191327B2 (en)	1979-06-29
FR2339619A1 (fr)	1977-08-26
BE850798A (fr)	1977-07-27
SE7700853L (sv)	1977-07-29
ZA77479B (en)	1977-12-28
PL101197B1 (pl)	1978-12-30

Legal Events

Date	Code	Title	Description
1982-09-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0000345B1 (fr)	1981-04-01	Dérivés phénoxybenzyloxycarbonyles substitués, leur procédé de préparation et leur utilisation comme insecticides et acaricides
EP0009566B1 (fr)	1981-09-09	Esters (thiono)(thiol)-phosphoriques (phosphoniques) de 2-cycloalkyl-pyrimidin(5)yl ou esters de leurs amides, procédé pour leur préparation et leur utilisation comme insecticides, acaricides ou nematicides
EP0000887B1 (fr)	1980-10-29	Esters et esteramides de pyrimidine-(4) d'acide (thiono)thiol-phosphorique (phosphonique) avec substituant cyclopropyl, leur procédé de préparation et leur application comme insecticides et acaricides
EP0007501A1 (fr)	1980-02-06	Esters et esteramides de pyrimidine-(4)yl d'acide (thiono)(thiol)-phosphorique(phosphonique) avec substituant cyclopropyl, procédé pour leur préparation, pesticides, procédé pour leur préparation, leur application et procédé pour combattre les parasites
DE2545392A1 (de)	1977-04-21	Benzimidoylthionothiolphosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
CH629817A5 (de)	1982-05-14	Verfahren zur herstellung neuer tert.-butyl-substituierter pyrazolyl(thiono)(thiol)-phosphor(phosphon)-saeureester bzw. -esteramide sowie ein insektizides, akarizides und nematizides mittel.
DE2629016C2 (de)	1983-11-10	O-(1-Fluor-2-halogen-äthyl)(thiono) phosphor(phosphon)-säureesteramide, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide, Akarizide und Nematizide
EP0012344B1 (fr)	1981-08-12	O-Pyrazolyl-4-O-éthyl-S-n-propyl esters de l'acide (thiono)thiol phosphorique, procédé pour leur préparation et leur utilisation comme pesticides
CH626230A5 (fr)	1981-11-13
CH635350A5 (de)	1983-03-31	Substituierte pyrimidinyl(thio)-phosphor(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide.
DE2545881C2 (de)	1985-08-29	0-Pyrazolopyrimidinthionothiolphosphorsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Bekämpfung von Insekten, Milben und Nematoden
CH646711A5 (de)	1984-12-14	Verfahren zur herstellung von neuen o-phenyldithiophosphonsaeureestern und ihre verwendung als insektizide, akarizide und nematizide.
EP0213393A1 (fr)	1987-03-11	Esters d'acides phosphoniques
EP0000388B1 (fr)	1980-11-26	Esters de pyridazinone d'acide (thiono)-phosphorique, leur procédé de préparation et leur application comme insecticides et acaricides
EP0000888A1 (fr)	1979-03-07	N-(aminométhylène)-(mono ou dithio) diester amides de l'acide phosphorique, leur procédé de préparation et leur application comme insecticides, acaricides et nématocides
CH633805A5 (de)	1982-12-31	Insektizides und akarizides mittel sowie verfahren zur herstellung neuer alkoxymethyl- bzw. alkylthiomethylsubstituierter pyrazolyl(thiono)(thiol)phosphor(phosphon)-saeureester bzw. -esteramide.
DE2714038A1 (de)	1978-10-19	Trifluormethylsulfonylphenylthiono (thiol)phosphorsaeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
DE3445465A1 (de)	1986-06-19	Pyrimidinyl-thionophosphorsaeureester
CH621794A5 (fr)	1981-02-27
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EP0335212A2 (fr)	1989-10-04	Amide ester d'acides thionophosphoriques
DE3811004A1 (de)	1989-10-19	Thionophosphonsaeureamidester
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